(S)-2-Tert-butoxycarbonylamino-3-(3-hydroxy-phenyl)-propionic acid

Base Information

• Chemical Name: (S)-2-Tert-butoxycarbonylamino-3-(3-hydroxy-phenyl)-propionic acid
• CAS No.: 90819-30-0
• Molecular Formula: C14H19 N O5
• Molecular Weight: 281.309
• Hs Code.: 2924299090
• European Community (EC) Number: 812-069-1
• Mol file: 90819-30-0.mol

Synonyms:90819-30-0;boc-l-m-tyrosine;(S)-2-TERT-BUTOXYCARBONYLAMINO-3-(3-HYDROXY-PHENYL)-PROPIONIC ACID;(S)-2-((tert-butoxycarbonyl)amino)-3-(3-hydroxyphenyl)propanoic acid;Boc-(S)-2-Amino-3-(3-hydroxyphenyl)propionic acid;(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(3-hydroxyphenyl)propanoic acid;(2S)-3-(3-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;Boc-L-phe(3-OH)-OH;BOC-M-L-TYR-OH;BOC-L-META-TYROSINE;(2S)-2-[(TERT-BUTOXY)CARBONYLAMINO]-3-(3-HYDROXYPHENYL)PROPANOIC ACID;BOC-PHE(3-OH)-OH;SCHEMBL3817907;FABANBOJFXYSHH-NSHDSACASA-N;MFCD01632034;AKOS015962384;N-BOC-3-HYDROXY-L-PHENYLALANINE;AM806687;AS-72506;CS-0136890;H10976;EN300-3372293;(S)-3-Hydroxyphenyl-2-tert-butyloxycarbonylaminopropionic acid;(S)-2-(TERT-BUTOXYCARBONYLAMINO)-3-(3-HYDROXYPHENYL)PROPANOIC ACID

Chemical Property of (S)-2-Tert-butoxycarbonylamino-3-(3-hydroxy-phenyl)-propionic acid

Chemical Property:

• PSA: 95.86000
• LogP: 2.30350
• Storage Temp.: Store at 0-5°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 281.12632271
• Heavy Atom Count: 20
• Complexity: 350

Purity/Quality:

98%min ^*data from raw suppliers

Boc-L-meta-tyrosine 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC(=CC=C1)O)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CC(=CC=C1)O)C(=O)O

Technology Process of (S)-2-Tert-butoxycarbonylamino-3-(3-hydroxy-phenyl)-propionic acid

There total 3 articles about (S)-2-Tert-butoxycarbonylamino-3-(3-hydroxy-phenyl)-propionic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 59.0%

di-tert-butyl dicarbonate (24424-99-5) + m-tyrosine (587-33-7,775-06-4,2180-37-2,32140-49-1,29562-33-2) → (S)-2-((tert-butoxycarbonyl)amino)-3-(3-hydroxyphenyl)propanoic acid (90819-30-0)

Guidance literature:

In ethanol; Ambient temperature;

DOI:10.1021/jm950717a

Reference yield:

D/L-3-hydroxy-phenylalanine (775-06-4,29562-33-2) → (S)-2-((tert-butoxycarbonyl)amino)-3-(3-hydroxyphenyl)propanoic acid (90819-30-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) α-chymotrypsin / 1.) enzymatic hydrolysis by α-chymotrypsin

2: triethylamine / 1.) DMF, 2 d, 2.) dioxan/water, 24 h

With triethylamine; α-chymotrypsin;

DOI:10.1002/recl.19841030402

Reference yield:

m-tyrosine (587-33-7,775-06-4,2180-37-2,32140-49-1,29562-33-2) + 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) → (S)-2-((tert-butoxycarbonyl)amino)-3-(3-hydroxyphenyl)propanoic acid (90819-30-0)

Guidance literature:

With triethylamine; 1.) DMF, 2 d, 2.) dioxan/water, 24 h;

DOI:10.1002/recl.19841030402

upstream raw materials:

m-tyrosine

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

di-tert-butyl dicarbonate

D/L-3-hydroxy-phenylalanine

Downstream raw materials:

Boc-L-m-Tyr-Gly-Gly-L-Phe-L-Leu-OEt

tert-butyl ((S)-3-(3-hydroxyphenyl)-1-(((1S,2R)-1-((3-iodobenzyl)-oxy)-1-phenylpropan-2-yl)(methyl)amino)-1-oxopropan-2-yl)-carbamate

tert-butyl ((S)-3-(3-hydroxyphenyl)-1-((S)-3-(((3-iodobenzyl)oxy)-methyl)-3,4-dihydroisoquinolin-2(1H)-yl)-1-oxopropan-2-yl)-carbamate

C₁₇H₂₃NO₅

Refernces

• 1、 Chen, Ping,Cheng, Peter T. W.,Alam, Masud,Beyer, Barbara D.,Bisacchi, Gregory S.,Dejneka, Tamara,Evans, Adelaide J.,Greytok, Jill A.,Hermsmeier, Mark A.,Humphreys, W. Griffith,Jacobs, Glenn A.,Kocy, Octavian,Lin, Pin-Fang,Lis, Karen A.,Marella, Michael A.,Ryono, Denis E.,Sheaffer, Amy K.,Spergel, Steven H.,Sun, Chong-Qing,Tino, Joseph A.,Vite, Gregory,Colonno, Richard J.,Zahler, Robert,Barrish, Joel C.. "Aminodiol HIV protease inhibitors. Synthesis and structure - Activity relationships of P1/P1′ compounds: Correlation between lipophilicity and cytotoxicity". . p. 1991 - 2007. Retrieved 2007/10/03.